tert-butyl 3-acetoxy-2-oxopropionate | 1447736-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 3-acetoxy-2-oxopropionate
• CAS: 1447736-38-0
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: MDECPVZHAKLKJO-UHFFFAOYSA-N

物化性质

• 沸点：
  258.5±23.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-acetoxy-2-oxopropionate 在 吡啶 、 氯化亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-ethyl 4-acetoxy-3-(N-methoxy-N-methylcarbamoyl)but-2-enoate
  参考文献：
  名称：

  Enynone dihydroxylation–cyclisation as a route to densely functionalised 3(2H)-furanone derivatives: an approach to the core of the zaragozic acids

  摘要：

  The synthesis of an advanced intermediate is described that could secure the polyoxygenated core of zaragozic acids and related natural products. The key strategy employs a two-step synthesis of the 3(2H)-furanone ring system by catalytic dihydroxylation-mercury(II)/acid-catalysed cyclisation with concomitant deprotection. The scope of the 3(2H)-furanone synthesis has been evaluated, and this ring system is shown to remain intact in multi-step reaction sequences. Access to novel, highly oxygenated 3(2H)-furanone derivatives has been achieved. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.125
• 作为产物：
  描述：

  丙烯酸叔丁酯 在 四氧化锇 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 水 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 96.75h， 生成 tert-butyl 3-acetoxy-2-oxopropionate
  参考文献：
  名称：

  Enynone dihydroxylation–cyclisation as a route to densely functionalised 3(2H)-furanone derivatives: an approach to the core of the zaragozic acids

  摘要：

  The synthesis of an advanced intermediate is described that could secure the polyoxygenated core of zaragozic acids and related natural products. The key strategy employs a two-step synthesis of the 3(2H)-furanone ring system by catalytic dihydroxylation-mercury(II)/acid-catalysed cyclisation with concomitant deprotection. The scope of the 3(2H)-furanone synthesis has been evaluated, and this ring system is shown to remain intact in multi-step reaction sequences. Access to novel, highly oxygenated 3(2H)-furanone derivatives has been achieved. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.125